Donerail, a 91-1 shot ridden by Louisville’s Roscoe Goose, exploded in the final sixteenth-mile for a half-length triumph over front-running favorite Ten Point.

2009: Mine That Bird (50.60-1); $103.20

The son of 2004 winner Birdstone, Mine That Bird is remembered for his odds as much as his performance in winning the the 135th running of the Kentucky Derby in 2009. A 50-1 shot ridden by Calvin Borel, the gelding rallied from 12 ½ lengths back a mile into the race to win running away on sloppy track for trainer Bennie "Chip" Woolley.

2005: Giacomo (50.30-1); $102.60

Off at 50-1 odds, the big, gray colt Giacomo appreciated Churchill Downs' long stretch and getting away from California's speed-favoring tracks, rallying from 18th to take the 2005 Kentucky Derby by a half-length over 70-1 shot Closing Argument.

1940: Gallahadion (35.20-1); $72.40

Call this the sweet Derby, the surprising victor Gallahadion campaigned by Milky Way Farm of Ethel V. Mars, widow of the candy-bar empire founder. Trainer Roy Waldron predicted Gallahadion would win, but few believed him, with Bimelech at 2-5 one of the shortest-priced favorites in Derby history. But Gallahadion, who had been second to Bimelech a week earlier in Churchill Downs’ Derby Trial, excelled over a cuppy track, getting a rail-skimming ride from jockey Carroll Bierman to beat Bimelech by 1 ½ lengths in the Derby.

1882: Apollo (32.96-1); $169.80 (on a $5 bet)

Apollo remains famous not so much for what he did — a half-length victory over Runnymede in a field of 14 — but for what he didn’t do: race at 2. Of all the so-called Derby “rules,” the granddaddy is that no horse has won the Kentucky Derby without having raced as a 2-year-old with the exception of Apollo.

1999: Charismatic (31.30-1); $64.60

When Charismatic captured the 125th Kentucky Derby by a neck over the late-running Menifee, it was another dramatic example of record-setting trainer D. Wayne Lukas taking chances. Charismatic prevailed and went on to win the Preakness but suffered a career-ending leg fracture while a close third in the Belmont Stakes.

1967: Proud Clarion (30.10-1); $62.60

Proud Clarion was a horse who got good at the right time and had the right set up, closing behind a torrid early pace under Bobby Ussery on their way to a length victory over Barbs Delight, with the great Damascus third. Proud Clarion went winless in three starts at 2 and didn’t run in a stakes of farther than seven-eighths of a mile until nine days before the Derby, finishing second in Keeneland’s Blue Grass. (Showing his hardiness, the Blue Grass came a week after Proud Clarion won a Keeneland allowance race, which came 11 days after winning his first allowance race at the Lexington track.)

1918: Exterminator (29.60-1); $61.20

Nicknamed “Old Bones” for his gangly physique, Exterminator is one of the most memorable Derby winners. The Derby was his first start at 3 and first in 10 ½ months – as well as his first time racing farther than 5 ½ furlongs. The gelding sold after his 2-year-old season to serve as a workmate for owner W.S. Kilmer’s champion Sun Briar. Exterminator began outworking Sun Briar, who didn’t make the Derby. Trainer Henry McDaniel convinced Kilmer to run the gelding in his place. With William Knapp aboard, Exterminator pressed the early pace, soon was dueling for the lead and ultimately edging away for a length victory over Escoba, with Viva America (who two weeks later won the Kentucky Oaks) another eight lengths back.

1953: Dark Star (24.90-1); $51.80

This Derby is known as much for the horse who lost — Native Dancer — than Dark Star, who handed “The Grey Ghost” his only defeat in 22 starts. But Dark Star had strong Louisville ties. His breeder, the late Warner L Jones Jr. of Hermitage Farm in Goshen, would become the first person to breed a Derby, Kentucky Oaks (Nancy Junior in 1967) and Breeders’ Cup (Is It True in 1988 Juvenile) winner, as well as serving on Churchill Downs’ board for more than 50 years, including overseeing the track’s revitalization during eight years as chairman.

Dark Star was purchased by mistake for $6,500 at Keeneland. Captain Harry Guggenheim had wanted to purchase two other similar-looking sons of Hermitage’s Australian import Royal Gem from Jones’ consignment and instead bid on Dark Star, the first in the ring. Guggenheim’s trainer, Moody Jolley, asked Jones to take the colt back, saying in return they’d bid at least as much on the two other colts. Jones refused, saying, “He’s over 21 and so are you.” Guggenheim was stuck with what proved the Derby winner as Dark Star, then trained by Eddie Hayward, led all the way under Henry Moreno to prevail by a head over Native Dancer.

1995: Thunder Gulch (24.50-1); $51.00

Thunder Gulch, bought privately by owner Michael Tabor, was a good 2-year-old who won the Fountain of Youth and Florida Derby to start his 3-year-old season. But after finishing fourth in Keeneland’s Blue Grass Stakes, Thunder Gulch was the least-discussed of trainer D. Wayne Lukas’ 1995 Derby triumvirate that included juvenile champion Timber Country and the top filly Serena’s Song. His win after beating Tejano Run by 2 ¼ lengths (with Timber Country another head back in third) ranks among the biggest overlays in Derby history. Gary Stevens, who had been riding in Hong Kong, gained the mount when his first Derby commitment was injured.